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A highly diastereoselective "super silyl" governed aldol reaction: synthesis of ?,?-dioxyaldehydes and 1,2,3-triols.

ABSTRACT: A highly diastereoselective approach for the synthesis of protected ?,?-dioxyaldehydes derived from (Z)-tris(trimethylsilyl)silyl "super silyl" enol ethers is described. A general and highly syn-stereoselective aldol reaction directed by the "super silyl" group catalyzed by triflimide (HNTf2) is developed providing ?,?-dioxyaldehydes and 1,2,3-triol fragments which can be a useful platform for the elaboration of natural and unnatural sugar derivatives.

SUBMITTER: Gati W

PROVIDER: S-EPMC5952264 | biostudies-literature | 2016 Jan

REPOSITORIES: biostudies-literature

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A highly diastereoselective "super silyl" governed aldol reaction: synthesis of α,β-dioxyaldehydes and 1,2,3-triols.

Gati Wafa W Yamamoto Hisashi H

Chemical science 20151006 1

A highly diastereoselective approach for the synthesis of protected α,β-dioxyaldehydes derived from (Z)-tris(trimethylsilyl)silyl "super silyl" enol ethers is described. A general and highly syn-stereoselective aldol reaction directed by the "super silyl" group catalyzed by triflimide (HNTf2) is developed providing α,β-dioxyaldehydes and 1,2,3-triol fragments which can be a useful platform for the elaboration of natural and unnatural sugar derivatives. ...[more]

PMID: 29861990

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